Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes

被引：64

作者：

Chen, Hao ^{[1
]}

Mondal, Arup ^{[1
]}

Wedi, Philipp ^{[1
]}

van Gemmeren, Manuel ^{[1
,2
]}

机构：

[1] Max Planck Inst Chem Energy Convers, Stiftstr 34-36, D-45470 Mulheim, Germany

[2] Westfalische Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany

来源：

ACS CATALYSIS | 2019年 / 9卷 / 03期

关键词：

C-H activation; cyanation; dual-ligand catalysis; palladium catalysis; nitriles; PALLADIUM-CATALYZED CYANATION; ELECTRON-DEFICIENT ARENES; AMINO-ACID LIGANDS; BOND CYANATION; ARYL HALIDES; ACTIVATION; FUNCTIONALIZATION; N; N-DIMETHYLFORMAMIDE; OLEFINATION; HETEROARENES;

D O I：

10.1021/acscatal.8b04639

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Aromatic nitriles are key structural units in organic chemistry and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting commercially available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches.

引用

页码：1979 / 1984

页数：11

共 73 条

[11] Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed Cyanation of Heteroarenes via C-H Functionalization [J].

Ding, Shengtao ;

Jiao, Ning .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (32) :12374-12377

[12] Direct cyanation of heteroaromatic compounds mediated by hypervalent iodine(III) reagents: In situ generation of PhI(III)-CN species and their cyano transfer [J].

Dohi, Toshifumi ;

Morimoto, Koji ;

Takenaga, Naoko ;

Goto, Akihiro ;

Maruyama, Akinobu ;

Kiyono, Yorito ;

Tohma, Hirofumi ;

Kita, Yasuyuki .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (01) :109-116

[13] Rhodium(III)-Catalyzed Direct Cyanation of Aromatic C-H Bond to Form 2-(Alkylamino)benzonitriles Using N-Nitroso As Directing Group [J].

Dong, Jiawei ;

Wu, Zhongjie ;

Liu, Zhengyi ;

Liu, Ping ;

Sun, Peipei .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12588-12593

[14] DIRECT CYANATION OF AROMATIC-COMPOUNDS .1. DIAZOTATION OF CYANAMIDE IN PRESENCE OF AROMATIC-COMPOUNDS [J].

EBERSON, L ;

NILSSON, S ;

RIETZ, B .

ACTA CHEMICA SCANDINAVICA, 1972, 26 (10) :3870-3874

[15] CYANATION OF AROMATIC HALIDES [J].

ELLIS, GP ;

ROMNEYALEXANDER, TM .

CHEMICAL REVIEWS, 1987, 87 (04) :779-794

[16] Remarkably High Reactivity of Pd(OAc)2/Pyridine Catalysts: Nondirected C-H Oxygenation of Arenes [J].

Emmert, Marion H. ;

Cook, Amanda K. ;

Xie, Yushu J. ;

Sanford, Melanie .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9409-9412

[17] Developing Ligands for Palladium(II)-Catalyzed C-H Functionalization: Intimate Dialogue between Ligand and Substrate [J].

Engle, Keary M. ;

Yu, Jin-Quan .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) :8927-8955

[18] Ligand-Accelerated C-H Activation Reactions: Evidence for a Switch of Mechanism [J].

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) :14137-14151

[19] Layered Double Hydroxides Derived ZnO-Al2O3 Supported Pd-Ag Catalysts for Selective Hydrogenation of Acetylene [J].

Gao, Xiaoping ;

Zhou, Yanan ;

Jing, Fangli ;

Luo, Jingjie ;

Huang, Qingsong ;

Chu, Wei .

CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (06) :1009-1015

[20] Rhodium-Catalyzed Directed C-H Cyanation of Arenes with N-Cyano-N-phenyl-p-toluenesulfonamide [J].

Gong, Tian-Jun ;

Xiao, Bin ;

Cheng, Wan-Min ;

Su, Wei ;

Xu, Jun ;

Liu, Zhao-Jing ;

Liu, Lei ;

Fu, Yao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) :10630-10633

← 1 2 3 4 5 6 7 8 →